JP2000507275A - 真菌感染の治療剤としての新規なトリアゾール類 - Google Patents
真菌感染の治療剤としての新規なトリアゾール類Info
- Publication number
- JP2000507275A JP2000507275A JP10534037A JP53403798A JP2000507275A JP 2000507275 A JP2000507275 A JP 2000507275A JP 10534037 A JP10534037 A JP 10534037A JP 53403798 A JP53403798 A JP 53403798A JP 2000507275 A JP2000507275 A JP 2000507275A
- Authority
- JP
- Japan
- Prior art keywords
- group
- triazol
- phenyl
- independently selected
- unsubstituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 206010017533 Fungal infection Diseases 0.000 title claims abstract description 18
- 208000031888 Mycoses Diseases 0.000 title claims abstract description 18
- 239000003814 drug Substances 0.000 title description 7
- 150000003852 triazoles Chemical class 0.000 title description 7
- 229940124597 therapeutic agent Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 169
- 238000000034 method Methods 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 230000003287 optical effect Effects 0.000 claims abstract 2
- -1 hydrogen Chemical group 0.000 claims description 116
- 150000002367 halogens Chemical class 0.000 claims description 101
- 229910052736 halogen Inorganic materials 0.000 claims description 99
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 96
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 87
- 125000001424 substituent group Chemical group 0.000 claims description 79
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 75
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 69
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 41
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 39
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 38
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 28
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 26
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000002541 furyl group Chemical group 0.000 claims description 23
- 125000001544 thienyl group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000002883 imidazolyl group Chemical group 0.000 claims description 20
- 125000002971 oxazolyl group Chemical group 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000001425 triazolyl group Chemical group 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 18
- 125000002950 monocyclic group Chemical group 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 claims description 16
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 208000015181 infectious disease Diseases 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 7
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 230000009885 systemic effect Effects 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- 125000000173 4-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC(F)(F)F)C([H])([H])* 0.000 claims description 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- IDTDXCBHVAIVLS-CXAGYDPISA-N (2r,3r)-2-(2,4-difluorophenyl)-3-(4-methylsulfonylpiperazin-1-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound N1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN(S(C)(=O)=O)CC1 IDTDXCBHVAIVLS-CXAGYDPISA-N 0.000 claims description 2
- AHDYWVQALCKYBY-VGOFRKELSA-N (2r,3r)-2-(2,4-difluorophenyl)-3-(4-phenylpiperazin-1-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1C1=CC=CC=C1 AHDYWVQALCKYBY-VGOFRKELSA-N 0.000 claims description 2
- RZMFJPJIFHREAX-SJKOYZFVSA-N (2r,3r)-2-(2,4-difluorophenyl)-3-[4-(2h-tetrazol-5-yl)piperazin-1-yl]-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1C1=NN=NN1 RZMFJPJIFHREAX-SJKOYZFVSA-N 0.000 claims description 2
- AJBVDSMJGJOJGD-OPAMFIHVSA-N (2r,3r)-2-(2,4-difluorophenyl)-3-[4-(4-nitrophenyl)piperazin-1-yl]-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1C1=CC=C([N+]([O-])=O)C=C1 AJBVDSMJGJOJGD-OPAMFIHVSA-N 0.000 claims description 2
- 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 claims description 2
- ZPMBBFLOJVNZMM-MZNJEOGPSA-N 4-[4-[4-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]piperazin-1-yl]phenyl]-1h-1,2,4-triazol-5-one Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1C(C=C1)=CC=C1N1C=NNC1=O ZPMBBFLOJVNZMM-MZNJEOGPSA-N 0.000 claims description 2
- MLIAHNZAOZRBQN-WLFVZUNHSA-N 4-[4-[4-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]piperazin-1-yl]phenyl]-2-(2-hydroxypropyl)-1,2,4-triazol-3-one Chemical compound O=C1N(CC(O)C)N=CN1C1=CC=C(N2CCN(CC2)[C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)C=C1 MLIAHNZAOZRBQN-WLFVZUNHSA-N 0.000 claims description 2
- QJHKAURLMUXUNQ-ROTAYESASA-N 4-[4-[4-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]piperazin-1-yl]phenyl]-2-[(2,4-difluorophenyl)methyl]-1,2,4-triazol-3-one Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1C(C=C1)=CC=C1N(C1=O)C=NN1CC1=CC=C(F)C=C1F QJHKAURLMUXUNQ-ROTAYESASA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 206010065764 Mucosal infection Diseases 0.000 claims description 2
- FIDQIKRPTVMGEH-WAIKUNEKSA-N [4-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 FIDQIKRPTVMGEH-WAIKUNEKSA-N 0.000 claims description 2
- XMYOPEAYNXPMAA-AUUYWEPGSA-N ethyl 4-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1[C@H](C)[C@@](O)(C=1C(=CC(F)=CC=1)F)CN1N=CN=C1 XMYOPEAYNXPMAA-AUUYWEPGSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- VTYOEXVLDDJNTC-UHFFFAOYSA-N 1-pyrrol-1-ylbutan-2-ol Chemical compound CCC(O)CN1C=CC=C1 VTYOEXVLDDJNTC-UHFFFAOYSA-N 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- HMVVEOHEOMGKGZ-MZNJEOGPSA-N (2r,3r)-2-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)-3-[4-[2-[[4-(trifluoromethyl)phenyl]methyl]tetrazol-5-yl]piperazin-1-yl]butan-2-ol Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1C(=N1)N=NN1CC1=CC=C(C(F)(F)F)C=C1 HMVVEOHEOMGKGZ-MZNJEOGPSA-N 0.000 claims 1
- VKJGJSBLWZQIQF-AUUYWEPGSA-N (2r,3r)-2-(2,4-difluorophenyl)-3-[4-(1,3-thiazol-2-yl)piperazin-1-yl]-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1C1=NC=CS1 VKJGJSBLWZQIQF-AUUYWEPGSA-N 0.000 claims 1
- RFBMAPFAHIZPTO-OPAMFIHVSA-N (2r,3r)-2-(2,4-difluorophenyl)-3-[4-(4-nitrophenyl)sulfonylpiperazin-1-yl]-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 RFBMAPFAHIZPTO-OPAMFIHVSA-N 0.000 claims 1
- KGZSMAXTOPYETR-MLGOLLRUSA-N (2r,3r)-2-(2,4-difluorophenyl)-3-piperazin-1-yl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound N1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCNCC1 KGZSMAXTOPYETR-MLGOLLRUSA-N 0.000 claims 1
- DUELOELTHKRUGH-OPAMFIHVSA-N (2r,3r)-3-[4-(4-aminophenyl)piperazin-1-yl]-2-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1C1=CC=C(N)C=C1 DUELOELTHKRUGH-OPAMFIHVSA-N 0.000 claims 1
- NACRJMDJHVACDT-OPAMFIHVSA-N (2r,3r)-3-[4-(4-aminophenyl)sulfonylpiperazin-1-yl]-2-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1S(=O)(=O)C1=CC=C(N)C=C1 NACRJMDJHVACDT-OPAMFIHVSA-N 0.000 claims 1
- RIOXXPUYWUFQFZ-ONOMSOESSA-N (2r,3r)-3-[4-[2-[(4-tert-butylphenyl)methyl]-1,2,4-triazol-3-yl]piperazin-1-yl]-2-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1C1=NC=NN1CC1=CC=C(C(C)(C)C)C=C1 RIOXXPUYWUFQFZ-ONOMSOESSA-N 0.000 claims 1
- FEWCMVADZXIQBY-PIIWDFAUSA-N (2r,3r)-3-[4-[2-[(4-tert-butylphenyl)methyl]tetrazol-5-yl]piperazin-1-yl]-2-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1CN([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)CCN1C(=N1)N=NN1CC1=CC=C(C(C)(C)C)C=C1 FEWCMVADZXIQBY-PIIWDFAUSA-N 0.000 claims 1
- CGRLFWAHWPZELM-UHFFFAOYSA-N 1-[2-[(4-tert-butylphenyl)methyl]tetrazol-5-yl]piperazine Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1N=C(N2CCNCC2)N=N1 CGRLFWAHWPZELM-UHFFFAOYSA-N 0.000 claims 1
- DCZSARMKKFQDTK-UHFFFAOYSA-N 2-[(2,4-difluorophenyl)methyl]-4-(4-piperazin-1-ylphenyl)-1,2,4-triazol-3-one Chemical compound FC1=CC(F)=CC=C1CN1C(=O)N(C=2C=CC(=CC=2)N2CCNCC2)C=N1 DCZSARMKKFQDTK-UHFFFAOYSA-N 0.000 claims 1
- DHSPCAYTGLOGHE-UHFFFAOYSA-N 2-butan-2-yl-4-(4-piperazin-1-ylphenyl)-1,2,4-triazol-3-one Chemical compound O=C1N(C(C)CC)N=CN1C1=CC=C(N2CCNCC2)C=C1 DHSPCAYTGLOGHE-UHFFFAOYSA-N 0.000 claims 1
- OYZQGVHUXYCLAM-UHFFFAOYSA-N 4-(4-piperazin-1-ylphenyl)-2-[[4-(2,2,3,3-tetrafluoropropoxy)phenyl]methyl]-1,2,4-triazol-3-one Chemical compound C1=CC(OCC(F)(F)C(F)F)=CC=C1CN1C(=O)N(C=2C=CC(=CC=2)N2CCNCC2)C=N1 OYZQGVHUXYCLAM-UHFFFAOYSA-N 0.000 claims 1
- ZLQGRYSVKZNACI-UHFFFAOYSA-N 4-(4-piperazin-1-ylphenyl)-2-[[4-(trifluoromethoxy)phenyl]methyl]-1,2,4-triazol-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1CN1C(=O)N(C=2C=CC(=CC=2)N2CCNCC2)C=N1 ZLQGRYSVKZNACI-UHFFFAOYSA-N 0.000 claims 1
- RPRRSVKSRLGERE-JIYROHSKSA-N 4-[4-[4-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]piperazin-1-yl]phenyl]-2-[(4-methoxyphenyl)methyl]-1,2,4-triazol-3-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N(C=2C=CC(=CC=2)N2CCN(CC2)[C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)C=N1 RPRRSVKSRLGERE-JIYROHSKSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 241001553014 Myrsine salicina Species 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims 1
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 83
- 239000007787 solid Substances 0.000 description 63
- 239000002904 solvent Substances 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 32
- 235000019439 ethyl acetate Nutrition 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 239000000741 silica gel Substances 0.000 description 24
- 229910002027 silica gel Inorganic materials 0.000 description 24
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78637697A | 1997-01-17 | 1997-01-17 | |
| US08/786,376 | 1997-01-17 | ||
| PCT/IB1998/000046 WO1998031675A1 (en) | 1997-01-17 | 1998-01-15 | New triazoles as therapeutic agents for fungal infections |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2000507275A true JP2000507275A (ja) | 2000-06-13 |
Family
ID=25138405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10534037A Pending JP2000507275A (ja) | 1997-01-17 | 1998-01-15 | 真菌感染の治療剤としての新規なトリアゾール類 |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0889881B1 (de) |
| JP (1) | JP2000507275A (de) |
| KR (1) | KR20000064644A (de) |
| AT (1) | ATE238286T1 (de) |
| AU (1) | AU740324B2 (de) |
| CA (1) | CA2249529A1 (de) |
| DE (1) | DE69813681D1 (de) |
| WO (1) | WO1998031675A1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010529985A (ja) * | 2007-06-15 | 2010-09-02 | コリア・リサーチ・インスティテュート・オブ・ケミカル・テクノロジー | 抗真菌活性を有するトリアゾール誘導体、その製造方法、及びこれを含む医薬組成物 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19617040C1 (de) * | 1996-04-27 | 1997-10-30 | Degussa | Verfahren zur Herstellung katalytisch wirksamer Beschichtungen für die Synthese von Cyanwasserstoff |
| CN1137102C (zh) * | 2000-05-24 | 2004-02-04 | 中国人民解放军第二军医大学 | 取代丙基三唑类抗真菌化合物和其盐类以及制备方法 |
| WO2002036587A2 (en) | 2000-11-01 | 2002-05-10 | Cor Therapeutics, Inc. | Process for the production of 4-quinazolinylpiperazin-1-carboxylic acid phenylamides |
| HUP0303249A3 (en) | 2001-02-22 | 2007-03-28 | Sankyo Co | Water-soluble triazole fungicide compounds and pharmaceutical compositions containing them |
| KR101577053B1 (ko) | 2013-11-20 | 2015-12-11 | 한국화학연구원 | 트리아졸 유도체를 포함하는 탈모 예방 및 발모 촉진용 조성물과 탈모 예방 및 발모 촉진용 화장료 조성물 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3508909A1 (de) * | 1985-03-13 | 1986-09-18 | Bayer Ag, 5090 Leverkusen | Piperazinylmethyl-1,2,4-triazolylmethyl-carbinole |
| GB8729083D0 (en) * | 1987-12-12 | 1988-01-27 | Pfizer Ltd | Triazole antifungal agents |
-
1998
- 1998-01-15 AT AT98900110T patent/ATE238286T1/de not_active IP Right Cessation
- 1998-01-15 JP JP10534037A patent/JP2000507275A/ja active Pending
- 1998-01-15 AU AU53362/98A patent/AU740324B2/en not_active Ceased
- 1998-01-15 KR KR1019980707355A patent/KR20000064644A/ko not_active Application Discontinuation
- 1998-01-15 EP EP98900110A patent/EP0889881B1/de not_active Expired - Lifetime
- 1998-01-15 WO PCT/IB1998/000046 patent/WO1998031675A1/en not_active Application Discontinuation
- 1998-01-15 DE DE69813681T patent/DE69813681D1/de not_active Expired - Lifetime
- 1998-01-15 CA CA002249529A patent/CA2249529A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010529985A (ja) * | 2007-06-15 | 2010-09-02 | コリア・リサーチ・インスティテュート・オブ・ケミカル・テクノロジー | 抗真菌活性を有するトリアゾール誘導体、その製造方法、及びこれを含む医薬組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0889881B1 (de) | 2003-04-23 |
| WO1998031675A1 (en) | 1998-07-23 |
| ATE238286T1 (de) | 2003-05-15 |
| EP0889881A1 (de) | 1999-01-13 |
| AU740324B2 (en) | 2001-11-01 |
| AU5336298A (en) | 1998-08-07 |
| KR20000064644A (ko) | 2000-11-06 |
| CA2249529A1 (en) | 1998-07-23 |
| DE69813681D1 (de) | 2003-05-28 |
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